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Thinking Outside the Box on Boston & Innovation

The inaugural Outside-the-Box Interactive (OTBi) program, held recently July 13 - July 17, featured three days of intensive conversations with top leaders, thinkers, and doers from the innovation and broader business communities. An extension of Outside the Box, Boston’s leading arts celebration, OTBi is designed to showcase that “entrepreneurship is an art form inside itself,” as Dan Shertzer of the festival’s lead sponsor Capital One said.  

Backed by a strong and eclectic group of collaborative sponsors — including Capital One, The Greater Boston Chamber of Commerce, WeWork, The City of Boston, General Electric, BostInno, and Boston Innovators Group (BIG) — the OTBi festival brought together leaders of emerging companies with established businesses and institutions.  The conversations were focused on Boston’s growth as a leading center of innovation, while also taking an honest look at how to make the City of Boston and its business climate stronger and more supportive for start-ups and entrepreneurs.

Below are some of the key points made over the three days by a few of the panelists at OTBi that focused on Boston’s strengths, where it needs improve to cultivate entrepreneurs, and the opportunities for the city to succeed as a leader in the innovation economy:


Throughout the program, panelists talked about Boston’s strengths as fertile ground for emerging companies. Here are just a few thoughts from speakers:

  • “Boston is so ‘mapable’.  You are only one introduction away from anyone you want to meet, yet the city is global in scale.” – Dave McLaughlin, General Manager, Eastern U.S. & Canada, WeWork

  • “In San Francisco, it is very hard to retain talent. Here in Boston, people are a lot more loyal, which is one of our most underappreciated strengths.” — Matt Hayes, principal, Point Judith Capital

  • “The number of institutions that produce cutting-edge research in Boston is unparalleled. Problems can be solved here.” — Neil Chheda, managing partner, Romulus Capital

  • “[Boston is an] obvious choice… Everything is here that you need to scale, including that it is very easy to be paired up with people, technical cofounders, and mentors — which isn’t the case elsewhere.” — Ellen Rubin, CEO, ClearSky Data

  • “Boston’s big advantage is that we have a large amount diversity.” — Michael Skok, founding partner, (Skok also pointed to our installed competitive advantages in infrastructure, security, network, and storage).


The speakers were also honest and frank about what Boston needs to do to continue on a successful trajectory. Here are a few key takeaways:

  • “Interactivity between small and large companies is still a huge opportunity,” said Greater Boston Chamber of Commerce President and CEO Jim Rooney. “While we were No. 1 for innovation on a recent report from 1776, we were 21 out of 26 for interactivity between small and large companies… We need to work on that.”

  • Boston needs to maximize opportunities for employee mobility whenever possible, suggested Skok.

  • “We need more media outlets telling the story of what’s happening locally,” noted Rob Go, partner at NextView Ventures.

  • “It is not clear that everyone knows everything Boston has to offer,” said Jodi Gernon, Director of the Arthur Rock Center for Entrepreneurship at Harvard Business School.

  • Boston needs to figure out how to be more attractive to consumer technology talent, suggested Drizly CEO, Nick Rellas (which Boston Globe technology editor Sara Castellanos noted we are on par with Maryland for talent on). Rellas also said that in Boston we need more “outsized swings.”


Throughout the three days, speakers were asked what the big opportunities were for Boston’s entrepreneurial community to corner. Here are just a few:

I’m looking forward to next year’s OTBi event. There, we will talk about even more successes coming out of Boston and the progress we’re making to build a stronger city for entrepreneurs at all scale.     


David Brown is VP of Innovation Leadership at the Greater Boston Chamber of Commerce. Follow him on Twitter: @dbskier